452324-48-0Relevant academic research and scientific papers
Synthesis and biological evaluation of endocyclic 2′,3′-didehydro-2′,3′-dideoxymethanocarba adenosine
Quirk Dorr, Danae R.,Vince, Robert
, p. 665 - 680 (2002)
This is the first report describing the synthesis and conformation of methanocarba nucleosides incorporating an endo (β-face) cyclopropyl at the 2′,3′ position of 2′,3′-didehydro-2′,3′-dideoxy carbocyclic nucleosides. These nucleoside isosteres have been shown to exist in a unique extreme eastern conformation. This prediction was confirmed by x-ray crystallography and high resolution NMR spectroscopy. As expected, the methanocarba adenosine compound was neither a substrate nor an inhibitor of adenosine deaminase. However, some of the compounds synthesized demonstrated moderate antiviral activity against HSV-1. The methanocarba adenosine and its triphosphate form were evaluated as inhibitors of HIV-1 reverse transcriptase.
The first synthesis of a 2',3'-methano carbocyclic nucleoside
Katagiri, Nobuya,Yamatoya, Yoshitsugu,Ishikura, Minoru
, p. 9069 - 9072 (1999)
A 2',3'-methano carbocyclic nucleoside, 9-(c-4-hydroxymethylbicyclo[3.1.0]hex-r-2-yl)-9H-adenine, has been efficiently synthesized from 2-azabicyclo[2.2.1]hex-5-en-3-one(ABH) in six steps involving 1,3-dipolar cycloaddition, photolysis, and adenine ring c
Synthesis of conformationally restricted 2′,3′-exo-Methylene carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template
Bhushan, Rashmi Gupta,Vince, Robert
, p. 2325 - 2333 (2007/10/03)
A series of 2′,3′-exo-methylene carbocyclic nucleosides was synthesized as potential antiviral agents. These compounds were built on a bicyclo[3.1.0]hexane template that exhibits a rigid pseudoboat conformation and is capable of maintaining an identical conformation in solid state and in solution. The structures of the synthesized compounds were elucidated by NMR and X-ray crystallography. All the compounds were tested as anti-HIV and anti-HSV agents. The chemically synthesized 5′-triphosphate analogue of 7 was evaluated directly as a reverse transcriptase inhibitor.
Preparation of 2′,3′-methano-carbocyclic nucleosides through the addition of diazomethane to 2-azabicyclo[2.2.1]hept-5-en-3-one
Ishikura, Minoru,Murakami, Atsushi,Katagiri, Nobuya
, p. 317 - 324 (2007/10/03)
The preparation of 2′,3′-methano-carbocyclic analogues of adenosine is reported. The addition of diazomethane to N-substituted 2-azabicylo[2.2.1]hept-5-en-3-one (ABH) (1) provided cyclopropane-fused ABH (3), which was converted to 2′,3′-methano carbocycli
